In January 2003, Chappelle’s Show, starring Dave Chappelle, premiered under controversy with a Frontline parody sketch with a character named Clayton Bigsby, a fictional black white supremacist. Comedy Central initially rejected the skit, citing its gratuitous use of the word “nigger” and other racial epithets (over 20 instances in the course of a nine-minute segment). Neal Brennan, co-creator of Chappelle’s Show, describes the fight, “Comedy Central didn’t think it was exemplary of what the show is and that was the most vicious fight we ever had with them because we were like, ‘This is exactly what the show is’” (Haggins 222). Dave Chappelle’s commitment to racial progress through his humor and his unwillingness to censor his art makes him a strong and incisive black vernacular intellectual.

The Clayton Bigsby sketch sets the tone for the next two-and-a-half seasons of Chappelle’s Show. The skit opens with a warning from fictional-journalist Kent Wallace, “WARNING: For viewers sensitive to issues of race, be advised that the following piece contains gratuitous use of the “N” word. And by “N” word, I mean Nigger. There, I said it” (“Frontline”). Kent Wallace’s exclamation of “There, I said it,” indicates the discomfort the sketch creates for a white audience. Chappelle’s “gratuitous use of the ‘N’ word” confronts the acceptability of the term. The sketch continues to play on the absurdities and issues surrounding the white supremacist movement and stereotypes of “blackness.” Clayton Bigsby, although black, represents the wrongs in “white” behavior.

Chappelle’s Show continually pushed the boundaries of what was acceptable on cable television but it became notorious for addressing issues of race especially uncomfortable matters such as the “N” word. Through sketches like “Roots Outtakes,” “The Racial Draft,” and “The Niggar Family,” as well as recurring segments such “Ask a Black Dude” and “Negrodamus” featuring Paul Mooney, a former writer for Richard Pryor, Chappelle’s Show brought the concerns of the black community to a diverse primetime audience. Despite its multi-racial viewers, Chappelle’s Show was anything but subtle with its delivery of racial humor. In a sketch entitled “Black Bush,” Chappelle, giving an interpretation of a black President Bush and his administration, blatantly points out the injustices and overt scrutiny that blacks face compared to whites. Chappelle asserts the public would be more critical of his administration if Bush were black. The skit aired amid controversy, like many Chappelle's Show sketches, during the 2004 election. While not a factor in the end of the series, “Black Bush” would be the last Chappelle-endorsed sketch to air on Comedy Central.

Chappelle’s humor clearly draws from his experience as a black man in America. This is evident in his stand-up special,Killin’ Them Softly. Born in Washington, D.C., Chappelle returns to the Capitol years after leaving the city where he claims to have “seen some shit.” Even prior to Chappelle’s Show’s success, the audience greets Chappelle with screams, cheers, and a standing ovation. He jokes to his hometown crowd about race relations, racial-profiling, police brutality, and life “in the ghetto.” He highlights the double standards of race by describing a white friend who confronts a cop under the influence of marijuana and gets out of a speeding ticket by saying “I’m sorry officer, I didn’t know I couldn’t do that” while blacks are wantonly killed by police and the injustice covered up by “sprinkling some crack” on blacks. Although Chappelle exaggerates, his musings point out fundamental wrongs within the law enforcement system and its treatment of blacks.

In a special, after the initial success of Chappelle’s Show, entitled For What It’s Worth, a predominately white, San Franciscan audience greets Chappelle with polite applause, a stark contrast to the zealous response from the black DC audience. He begins by saying that he knows how they manage to get along so well because they “put the niggers on the other side of that bridge.” This shows that Chappelle will not restrain his material due to the demographics of the room. He addresses the injustice towards blacks since the founding fathers, referring to money as “baseball cards of slave owners.” He also riffs about racial bias in the trials of Kobe Bryant, R. Kelly, and even Michael Jackson, blaming black reaction to the OJ Simpson trial for the “black-celebrity witch-hunt.” However, Chappelle claims when he visits schools he says to black children, “You need to focus. You gotta stop blaming white people for your problems and you’ve got to learn to rap, play basketball, or something! Nigga, you’re trapped! Either that or sell crack! Those are your only options!” His joke contains the common theme of uplift and despite some negative stereotypes, it resonates with the black audience who not only understand the need to control their own destiny but also the limited options that white-oppression has given them.

Chappelle’s Show came to an abrupt and mysterious end in its third season when Chappelle left for Africa to escape the pressures of fame as well as his disillusionment with the direction of the show, wondering if he was “reinforcing stereotypes” that he was trying to combat. A “Racial Pixies” sketch, where Chappelle portrays pixies of different races giving stereotypical advice on how to act, reportedly led to Chappelle’s departure when a white crew-member laughed in a way that made Chappelle feel uncomfortable with the material. Chappelle’s “Black Pixie” is particularly regressive. Chappelle plays himself and a pixie made up in blackface. The pixie bugs Chappelle on an airline flight when he is given the choice between ordering chicken or fish, telling him to "order a big bucket" and proceeds to shingle dance. Chappelle orders fish, angering the pixie, but the flight attendant tells him they are out of fish. Chappelle asks how the chicken is prepared and the attendant replies, "fried," and the pixie exclaims "hallelujah!" The pixie summons a minstrel banjo player, played by Mos Def, “to celebrate.” A passenger offers to switch his fish dinner with Chappelle’s, which Mos Def’s pixie exclaims might be catfish and they begin to sing. Given the obnoxiously bigoted portrayal of regressive stereotypes, it is no surprise that Chappelle claims he felt that the unnamed “white crew-member” was “laughing at me instead of laughing with me.”

Filmed two years before the infamous “Pixie Sketch,” Dave Chappelle’s Block Party is anything but regressive. Chappelle is at the height of his game, having recently captured the famous $55 million dollar deal (which he later returns after his Africa departure) for Season 3 of Chappelle’s Show. Most of the film consists of music from Chappelle’s Show musical guest regulars such as Mos Def, The Roots, Kanye West, Talib Kweli, dead prez, and other artists that Chappelle believes “say what nobody else is saying and what needs to be said.” Between scenes, Chappelle jokes around with the “regular people” who he claims are the “reason [he is] in this business.” While Chappelle’s humor may be incisive, bold, or even regressive, his comedy ultimately serves to uplift the black community while building bridges to other races with his widespread appeal. As his reemergence in the stand up circuit post-Chappelle's Show illustrates, Chappelle’s talent is here to stay.